Acetic Acid → HCID 18541324, compound

HRID 411738Notes

Reaction equation

HRID 411738 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:3]=1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[C:19]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1.O>[CH2:24]([O:23][C:21](=[O:22])[C:20](=[CH:10][C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][C:3]2[C:2]([Cl:1])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:18])=[CH:7][CH:8]=1)[C:19]([O:27][CH2:28][CH3:29])=[O:26])[CH3:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 7354664-[(2,6-dichlorobenzyl)oxy]benzaldehyde

Product 1

HCID 18541324HCID 18541324, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(2,6-dichlorobenzyloxy)benzaldehyde (5.62 g, 20 mmol) and diethyl malonate (3.52 g, 22 mmol) in benzene (75 mL), were added piperidine (90 μL) and glacial acetic acid (0.25 mL). After refluxing for 24 h with azeotropic water removal, the cooled reaction was concentrated in vacuo then partitioned between ether and water. The organic extract was washed successively with 1N hydrochloric acid, saturated sodium bicarbonate solution, water, brine and dried (MgSO4). Removal of volitiles in vacuo afforded the crude title compound (8.35 g, 97%) which was used in the next step without farther purification.

Workup

  1. customthe cooled reaction
  2. concentrationwas concentrated in vacuo
  3. customthen partitioned between ether and water
  4. extractionThe organic extract
  5. washwas washed successively with 1N hydrochloric acid, saturated sodium bicarbonate solution, water, brine
  6. dry with materialdried (MgSO4)
  7. customRemoval of volitiles in vacuo

Sources & evidence

ORD record
ord-08e06f6473a74a6d97f90567fea30d64
Source dataset
uspto-grants-2003_05
Patent number
US06559179B1

Reaction notes

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